Photos not sending through iMessage when on Wi-Fi?

I have an iPhone 4S running iOS6 (although I was having this issue pre-iOS6). My iPhone sends iMessages, so long as they are text, fine, delivers read receipts, everything fine when I'm on Wi-Fi. It used to send photos on all the Wi-Fi connections I typically use (home, campus, favorite coffee shop, etc.) but about a week prior to iOS 6 it decided it would no longer send photos via iMessage. When I want to send a photo I have to turn off my wireless, and send the photo on data. Then I turn wireless right back on and resume sending texts via iMessage. I have no issues with other Wi-Fi functions - web browsing, etc. Is unaffected.
SMS and MMS are on. My iMessaging is directly linked to my phone number, not my Apple ID, if that makes a difference?

Hoping someone can help with this, especially since it appears its not my wireless signal thats the problem as my iPhone has decided to do this over multiple different wireless signals it used to not have an issue with.

Have been playing around at home for a few weeks now, I have an ipad2, and qty 2x iPhone5's NONE of them will send IMessages or Photostream desnt work either on my home Wi-Fi setup but work fine on any other Wi-Fi's!

I have reset my ipad2 back to factory defaults and I even tried setting up a NEW iTunes account but neither of these things worked.

So as a last resort i have just put in a new ADSL2 (Melbourne, Australia) modem and Wi-Fi that I had sitting around, both different brands and have gotten it working!

I can now send iMessages with pictures on Wi-Fi and my photo stream has started working again. I can't work out why my old setup doesn't work as I tried factory restoring the modem and nothing.

Old hardware;
- dlink DSL-502T (ADSL2 modem)
- dlink DIR-600 (Wi-Fi hotspot)

New hardware;
- Linksys AM300 (ADSL2 modem)
- Sonicwall sonicpoint G (Wi-Fi hotspot)

Going to see if i can get the newer dlink Wi-Fi to work with my Linksys modem next.

  • Why is my iphone 5 sending imessages through my email This is doing my head in I recently updated my iphone to the new IOs and its not sending my imessages through my number anymore its doing it through my apple id help to change this back please.
  • Why is my IMessage sending but not delivering? I have an iPhone 4 and I'm trying to text a friend and I text them and it says delivered but then a few seconds later it says not delivered. It is doing it to only this one person and it randomly started doing this. When they text me it comes in as text. How can I fix this? What is wrong?
  • Sending pictures through text message? My first smartphone was an iPhone 4 and I didn't have data so I could only send pictures through iMessage. Now I have a Moto G 3rd Gen, still no data (don't want it). But I thought I could finally be able to send pictures? It's saying I need data even though my plan says unlimited text and picture messaging… Is this a thing?
  • My photos are not sending in group messages, but are sending in individual messages? I'm with Straight Talk Wireless. At first my pictures were sending in the group message but now they are not. I don't know what's wrong, all my settings are what they are suppose to be, and I'm currently on an iPhone 5s IOS 8.4.